This invention relates to quinolinesulfonamides which are useful as agricultural chemicals.
French Pat. No. 1,468,747 discloses the following para-substituted phenylsulfonamides, useful as antidiabetic agents: ##STR1## wherein R=H, halogen, CF.sub.3 or alkyl.
Logemann et al. Chem. Ab., 53, 18052 g (1959), disclose a number of sulfonamides, including uracil derivatives and those having the formula: ##STR2## wherein R is butyl, phenyl or ##STR3## and R.sub.1 is hydrogen or methyl. When tested for hypoglycemic effect in rats (oral doses of 25 mg/100 g), the compounds in which R is butyl and phenyl were most potent. The others were of low potency or inactive.
Wojciechowski, J. Acta. Polon. Pharm. 19, p. 125-5 (1962) [Chem. Ab., 59 1633 e] describes the synthesis of N-[(2,6-dimethoxypyrimidin-4-yl)aminocarbonyl]-4-methylbenzenesulfonamide: ##STR4## Based upon similarity to a known compound, the author predicted hypoglycemic activity for the foregoing compound.
Netherlands Pat. No. 121,788, published Sept. 15, 1966, teaches the preparation of compounds of Formula (i), and their use as general or selective herbicides, ##STR5## wherein R.sub.1 and R.sub.2 may independently be alkyl of 1-4 carbon atoms; and
R.sub.3 and R.sub.4 may independently be hydrogen, chlorine or alkyl of 1-4 carbon atoms. PA1 R'=Et, Pr, Me.sub.2 CH, Bu ##STR10## in 2, 3 and 4 position. PA1 R'=alkylcarbamoyl, cyclohexylcarbamoyl, arylcarbamoyl, CSNHCH.sub.2 CH=CH.sub.2, CONHC.sub.6 H.sub.4 Cl-p, alkylthiocarbamoyl, H, COEt; PA1 R.sup.2 =H, Me; PA1 X=NH, NMe, O, S, NEt; and PA1 n=0,1. PA1 W is oxygen and sulfur. PA1 R.sub.2 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 R.sub.3 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.4 alkyl; PA1 R.sub.6 is C.sub.1 -C.sub.4 alkyl or CF.sub.3 ; PA1 n is 0, 1 or 2; PA1 X is C.sub.1 -C.sub.2 alkyl, C.sub.1 -C.sub.2 alkyl substituted with OCH.sub.3, CF.sub.3, C.sub.1 -C.sub.3 alkoxy, N(CH.sub.3).sub.2, NHCH.sub.3, NH.sub.2, or SCH.sub.3 ; PA1 Y is CH.sub.3, OCH.sub.3 or Cl; PA1 Z is CH or N; and PA1 W is O or S; PA1 (1) A is in the 5 or 8 position of the quinoline ring; PA1 (2) when R.sub.1 is NO.sub.2, CO.sub.2 R.sub.2, S(O).sub.n R.sub.3, SO.sub.2 NR.sub.4 R.sub.5, SO.sub.2 N(OCH.sub.3)CH.sub.3 or OSO.sub.2 R.sub.6, then R.sub.1 is at the 6-position when A is at the 5-position, and R.sub.1 is at the 7-position when A is at the 8-position of the quinoline ring; SO.sub.2 N(OCH.sub.3)CH.sub.3 or OSO.sub.2 R.sub.6, then R.sub.1 is at the 6- or 7-position of the quinoline ring; PA1 (3) the total number of carbon atoms of R.sub.4 and R.sub.5 is less than or equal to 5; and PA1 (4) when Y is Cl, then Z is CH and X is NH.sub.2, NHCH.sub.3, N(CH.sub.3).sub.2 or OCH.sub.3. PA1 (1) Compounds of the generic scope where A is in the 8-position of the quinoline ring; R.sub.1 is H, Cl, Br, OCH.sub.3, CO.sub.2 CH.sub.3, or NO.sub.2 ; and W is O. PA1 (2) Compounds of Preferred (1) where R.sub.1 is in the 7-position of the quinoline ring; PA1 (3) Compounds of Preferred (2) where A is ##STR19## (4) Compounds of Preferred (3) where X is CH.sub.3 or OCH.sub.3 ; and (5) Compounds of Preferred (4) where R.sub.1 is H, Cl, Br or OCH.sub.3. PA1 R.sub.2 is C.sub.1 -C.sub.4 alkyl, C.sub.3 -C.sub.4 alkenyl, CH.sub.2 CH.sub.2 Cl or CH.sub.2 CH.sub.2 OCH.sub.3 ; PA1 R.sub.3 is C.sub.1 -C.sub.4 alkyl; PA1 R.sub.4 and R.sub.5 are independently C.sub.1 -C.sub.4 alkyl; PA1 R.sub.6 is C.sub.1 -C.sub.4 alkyl or CF.sub.3 ; PA1 n is 0 or 2; PA1 X.sup.1 and Y.sup.1 are independently Cl or Br; and PA1 Z is CH or N; provided that PA1 (1) when R.sub.1 is NO.sub.2, CO.sub.2 R.sub.2, S(O).sub.n R.sub.3, SO.sub.2 NR.sub.4 R.sub.5, SO.sub.2 N(OCH.sub.3)CH.sub.3 or OSO.sub.2 R.sub.6, the R.sub.1 is in the 7-position of the quinoline ring; and PA1 (2) the total number of carbon atoms of R.sub.4 and R.sub.5 is less than or equal to 5.
Compounds of Formula (ii), and their use as antidiabetic agents, are reported in J. Drug. Res. 6, 123 (1974). ##STR6## wherein R is pyridyl.
U.S. Pat. No. 3,689,549 (Sept. 5, 1972) to R. P. Williams discloses "heterocyclic sulfonamides wherein the heteroatoms are inert can also be used, e.g., compounds having the furan, thiophene or pyridine nucleus," in the production of sulfonyl isocyanates from sulfonamides in a sulfolane solvent.
B. G. Boggiano, V. Petrow, O. Stephenson and A. M. Wild, in Journal of Pharmacy and Pharmacology 13, 567-574 (1961) disclose the following compounds which were tested for hypoglycemic activity. ##STR7## where ##STR8## is in 2 or 3 position.
J. Delarge in Acta Pol. Pharm. 34, 245-249 (1977) discloses the following compounds as mild antiinflammatory agents. The 4-aryl-3-sulfonamides were disclosed as strong diuretics. ##STR9## R=3-, 4-, 5-, 6-Me, 2-, 4-, 6-Cl, 3-Br, 4-ET.sub.2 N, 4-Me.sub.2 CHNH, 4-(3-ClC.sub.6 H.sub.4)NH, 4-(3-CF.sub.3 C.sub.6 H.sub.4)NH
German Pat. No. 2,516,025 (Nov. 6, 1975) (to J. E. Delarge, C. L. Lapiere and A. H. Georges) discloses the following compounds as inflammation inhibitors and diuretics. ##STR11## R=C.sub.6 H.sub.4 R.sup.3 (R.sup.3 =Cl, CF.sub.3, Me, MeO, H, Br, F, NO.sub.2, Et, NH.sub.2), Et, iso-Pr, 4-methylfuryl, C.sub.6 H.sub.3 Cl.sub.2 -, C.sub.6 H.sub.3 (CF.sub.3)Cl;
U.S. Pat. No. 3,346,590 (Oct. 10, 1967) (to K. Dickere and E. Kuhle) discloses the following pyridinesulfonyl isothiocyanates as novel compounds. ##STR12##
U.S. patent application Ser. No. 083,753 (now abandoned) discloses herbicidal pyridine sulfonylureas of Formula (iii). ##STR13## where R is ##STR14## R.sub.3 and R.sub.4 are independently H or CH.sub.3 ; Z is CH or N; and
U.S. patent application Ser. No. 033,752 discloses herbicidal isothioureas of Formula (iv). ##STR15## where R is ##STR16## R.sub.3 is C.sub.1 -C.sub.5 alkyl; and R.sub.4 is H or CH.sub.3.
The presence of undesired vegetation causes substantial damage to useful crops, especially agricultural products that satisfy man's basic food and fiber needs, such as cotton, rice, corn, wheat, soybean and the like. The current population explosion and concomitant world food and fiber shortage demand improvements in the efficiency of producing these crops. Preventing or minimizing the loss of a portion of such valuable crops by killing or inhibiting the growth of undesired vegetation is one way of improving this efficiency.
A wide variety of materials useful for killing or inhibiting (controlling) the growth of undesired vegetation is available; such materials are commonly referred to as herbicides. The need exists however, for still more effective herbicides that destroy or control weeds without cuasing significant damage to useful crops.